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I’ll probably appear to be a bit fixated on this topic, but I wanted to share a conversation from last night while it’s still fresh in my mind.

My wife revisited the “jealousy” topic (see my prior post) after we went to bed. She wanted to talk about it more, in some detail. It surprised me.

She started out saying she wanted to be sure she understood how I thought I would feel if she were to have sex with another guy. “So, you’re telling me you wouldn’t be jealous?” she asked.

“Well, like I said before, if it threatened our relationship, like if you wanted him instead of me as a life partner, then yes, I think it would be terribly hurtful for me. Not in a erotic humiliation sort of way, but in a severe depression and life sucks sort of way.” I continued, “But if it was just sex and not a deeper, emotional relationship, then… I don’t think I’d be jealous.”

She still seemed surprised. “I just don’t get that,” she said.

I asked her “Well, how would you feel if I had an affair?” Her response was immediate and firm. “Oh, that’s easy. I’d leave you immediately and we would get a divorce as soon as possible. I hope that’s clear. Is it?” I said “Yes, Ma’am, very clear. That will never happen.”

There is no doubt that this is a female-led relationship, that she is the dominant, and that I am her submissive.

“Let’s walk through a scenario,” she said. “You imagine it happening for real, and tell me how you feel.”

She continued. “You come home from work someday, and things look a bit messier than usual in the house, like maybe I’ve been distracted most of the day. You don’t find me downstairs, but hear something upstairs and come into our bedroom. There you see me naked on the bed with another man. We’re having sex, and the room smells like we’ve been doing it for hours. I don’t hear you, as I’m just about to orgasm again, and I do, making quite a bit of noise. Then I do notice you, and tell you to shut up and sit down. What do you do?”.

I said “I’d quietly sit down, without saying ‘Yes, Ma’am, right away’ as you’ve instructed, because you said to shut up.” She replied “Very good. And how would you feel?”

I pondered this, trying to put myself into this mythical situation. It was difficult to separate the idea of this really happening from a fantasy (one I’ve had many times). I answered her, “Well, I would feel surprised, shocked, and maybe a little hurt. But I’d also feel somewhat good that you were enjoying yourself so much, being sexually satisfied by him.”

Then she asked “How about if he was giving me oral sex? How would you feel about that?” That answer seemed easier: “I’d feel a little more hurt by that, since I really enjoy going down on you, and it’s something I can still do.” She didn’t miss the opportunity to rub it in, saying “Yes, I guess that is the one way you can still satisfy me sexually. We both know that, thanks to the hormones, tiny is more worthless than ever.”

She put her hand down my pajamas to check tiny’s status and said “This is turning you on, isn’t it?” I had to admit that it was (it always does). The answer to her question was obvious, but despite that, we both knew that there wasn’t enough there for me to sexually satisfy her. My size, thickness, and firmness has substantially decreased; a year of feminizing hormones will do that.

She rolled over onto her stomach, and put a hand down between her legs. She made a point of telling me “I’m going to masturbate now, thinking about having sex with a black guy I met at a swingers party before I met you. He had a magnificent cock. I gave him a bj back then. I might still have his email address. It might be time to reconnect. Mmmmm.” She started moaning and bucking her hips. I put my hand on her thigh to feel her gyrate until she came, relaxed, and got quiet.

It feels like I’ve just gone past that point — where those who want to be cuckolded suddenly realize that this might not be just a fantasy anymore, and that it’s truly out of their control. Maybe she’s just mindfucking me again. But what if she isn’t?

Mistress gave me an orgasm on Friday. It had been 48 days since my last one, and I was securely locked up for the last 35 days.

I had a doctor’s appointment the next day, one that included a genital exam. So she wanted me to take it off (I would have been fine leaving it on, and it wouldn’t have gotten in the doctor’s way at all). Mistress masturbated me while biting my chest. It didn’t take me long.

I don’t think she realized it, but she stopped stroking right as I started to cum. I begged her to keep going, and after a short pause she did. Fortunately I had another climax and got to fully unload. There was a ton of fluid. No surprise, I suppose, since it had been almost 7 weeks of celibacy for me. I was worried that she was going to give me a “ruined orgasm”. That would have really sucked!

The doctor appointment was with my endocrinologist — the one who will oversee the female hormones that I am likely to be on in a week or two. She did a health history, advised us about the risks, did a quick physical — including the genital exam and a prostate exam with Mistress watching! Yesterday I had some blood drawn for lab tests, which should show me healthy and ready for hormones. About a week for those test results.

Mistress told me today she’s looking forward to me having a pussy. She has plans to fist me in a variety of ways, and was telling me details today. She want to fist my pussy and the pussy of a friend of ours. She’s done us both before, but obviously one of her hands was up my ass then, the other in our friend’s vagina.

She also wants to double-fist me – one in my pussy, and one in my ass. And she’s talked about the various dildos she plans to use to fuck me. (I wish she’d fuck my ass now!).

Another thing she plans to do is have people watch while she sews my labia lips together (explicit image here). And yes, she’s completely serious and I fully believe she will do it.

Not sure what she plans to do about keeping me in chastity once my easy-to-secure cock becomes a tempting pussy. She’s never liked the full waist-belt style metal chastity belts, but maybe she’ll end up locked me into one. Not sure how else she’ll be able to control access to my eventual clitoris otherwise.

For the moment Mistress has decided to leave me out of the cage. It will help me crossdress more effectively (and comfortably). A few months back you may recall that I signed a written chastity contract with her. It clearly specified that I must avoid all masturbation or stimulation of my genitals, and that I have turned over all of my sexuality and control of my cock and balls to her. So even though I’m not locked in the JailBird, I am still “in chastity”. And I fully intend to be faithful to her and our contract.

My spouse, Mistress, and keyholder took me to a kinky party yesterday, but left me in chastity. However, I was luckier than another guy we saw there.

It’s been over 5 weeks since my last orgasm, and 23 days of continuous lock-up in my JailBird + PA-lock. Last night, though, I watched a poor guy get teased to an unbelievable degree — and he’s been denied orgasms for 57 days.

His owner had bound him (naked of course) to a suspended leather sling with plastic wrap in the dungeon at this party. She then proceeded to sexually tease him for a solid hour, stroking his cock and stopping before he could orgasm. A small audience watched.

If he got too close, she would give him some “distracting pain” to “help” him avoid an orgasm. Things like slapping the head of his cock really hard with her hand, or grabbing his balls and squeezing them hard. He got close to cumming time after time after time. But he never spurted.

I’m not sure what their agreement was, but he was begging not to orgasm. In the end he got his wish, but not before what seemed like an unbearable amount of substantial penile stimulation. His owner knew how to get him off, her hand-job technique was clearly effective. He was hard the whole time, and making the most interesting noises throughout.

His scene was still going on when Mistress decided it was time for me to submit to her and our friend. She took out our lightest leather bondage hood and secured it tightly around my head. It has a snap-on blindfold and a snap-in gag, which she left out initially.

She led me over to a bondage table, with webbing for dozens of straps to bind the limbs and torso. I’d been on it before, and knew what to do. I removed my clothes and got in position to be tied down.

Mistress kept it simple, using just 5 of the thick nylon straps to secure my wrists, ankles, and waist. Our friend joined us, and I was then blindfolded and gagged. They wasted no time and started tickling me mercilessly. I recognized the voice of the owner of the other chaste male who was tickling my feet and really enjoying watching me thrash and squirm and (try to) yell. Mistress and our friend were at my sides tickling my ribs. I felt completely out of control as my body tried uselessly to move away from the excessive stimulation. They all seemed to have a great time.

Eventually they stopped, and Mistress directed our friend to help calm me down with “smoothing” hand motions on my skin. My breathing slowed, and I settled down.

Then I felt her start stimulating my nipples. Mistress whispered to me that she wanted me to orgasm in front of everyone in our new special way. I nodded to let her know I understood and would try. At this point we’ve only done it a few times, and I wasn’t sure I could do it there in the dungeon. But, wanting to please her, I was going to try.

The nipple stimulation continued, and I continued my deep breathing, focusing not on my cock but on the growing sense of sexuality throughout my body. My cock doesn’t get very hard during these experiences — it’s not a penis-based orgasm. I felt the sensual energy building inside of me.

Then she was biting me. Mistress’ teeth dug into the flesh of my chest as her fingers continued their very arousing motions on my nipples. Then our friend began biting me on the other side, and licking my nipple as she sucked my breast skin into her mouth. The pain mixes with the pleasure for me, taking me deeper and farther.

I heard Mistress ask me if I needed more, and I nodded. The two of them continued stimulating me and biting, until finally I went over the edge. My body shuddered and I felt flushed. I strained against my bonds as I tried to arch my back and spread my legs as the orgasm spread through me. They continued stimulating me and pushing me on, until I went limp. Mistress reminded me to continue breathing as I recovered.

I wasn’t sure what to expect at the party, but it was a very nice scene. Mistress seems very interested in exploring this alternate way of pleasure for me, and she continues to show no interest in my cock. I think it’s her way of encouraging my new female sexuality to emerge.

A number of people seemed surprised when I got undressed before the scene. But I wasn’t sure if that’s because they didn’t realize I was a guy (I was wearing a new hot dress for the party), or if they hadn’t seen a stainless steel chastity cage like mine before. Either way, I was fully on display for quite a while. Being blindfolded, I have no idea who was watching during our scene.

A short while later I was dressed again, fetching Mistress some food and then massaging her feet as she chatted with others. A little while later we were back in the dungeon watching several other scenes, while I was Mistress’ footstool. It was a wonderful evening.

Mistress and I entertained her sister today. It was the first time I was dressed in my female role in front of a family member. It went very well.

We were eating a late lunch out on our deck, and the two of them were talking about men and relationships. Somehow the conversation turned to black men, and Mistress made me quite embarrassed. She told her sister about the man adjacent to her workplace, how attractive he is and what a nice sexual partner he would make. He’s the one she teases me about having sex with a lot (I’ve blogged about that many times before).

Her sister thought she was just lightly teasing me, so Mistress went further. She said “just because my spouse won’t be able to please me like a man, that doesn’t mean I won’t get any.” Her sister laughed like it was a joke, and Mistress just sat there with a smile. I blushed like I had too much makeup on. “After all,” Mistress clarified, “I’m not a lesbian, I’m bisexual.”

At another point in the conversation Mistress told her sister “Chastity isn’t so bad,” when talking about her sister not dating for a while. Of course that was a subtle dig at my locked up cock.

After her sister left, we stayed on the deck to chat. I found an inchworm and we watched it for a while. Mistress named it “tiny”, for obvious reasons. “Go, tiny, go!” she said as it slowly moved across the table. At one point I remarked that he was “straight up”, and her quick reply was “Well, I haven’t seen anything like that in quite some time.” I observed that it was by her choice, and she just smiled.

Mistress used me for her own orgasm this morning. I really enjoy being used like an object that she uses for her own pleasure. I mentioned to her that it turned me on. She said she didn’t notice, and that it doesn’t matter anyway. I love it that she’s right — that her sexual pleasure matters and mine doesn’t.

It’s been 12 days so far in chastity this time, and to be honest, I’ve hardly noticed. It’s just the way things are now.

Sitting to pee is just second nature, I hardly think about it. About the only time it registers is around showering. And even then it’s just procedural: wash it, dry it, put a little lube around the base ring.

You’d think having a tight stainless steel locked to your penis would be a bigger deal.

We’ve had the JailBird for almost 4 months now, and I’ve worn it at least 95% of that time. Male orgasms appear to be a thing of the past now. They are simply not interesting to her at all any more. I don’t even find I crave them that much, although I suppose I could easily fall back into the masturbation habit. I don’t want to, though.

Now that I’ve experienced (what seems to be) female orgasms, there’s just no comparison. The last time we did that, tiny (her name for my cock) was only a little bit hard, barely at all. Mistress stimulated my nipples, touched and rubbed me elsewhere on my upper body, and guided me with her words to relax into building wave after wave of sensation. Eventually I went over the threshold into this extremely blissful state, with my whole body participating in the sensory experience. It’s hard to describe, but oh so wonderful.

Mistress prefers me to have these “girlgasms” because I don’t get all cranky and grumpy afterwards. Right after, all I want to do is get close to her — even cuddling right next to her doesn’t feel close enough. I just crave feeling her next to me. The next few days I’m extra attentive and loving to her, so appreciative and present. I think we both prefer it this way.

And this works out pretty well with the whole sex-change business. I’m feeling impatient lately. I want to get on with this Becoming a Woman thing. I mentally put myself in that role walking around work every day. Even though am not ready to approach them yet to discuss it, part of me is so ready to come out — all the way out.

Over a dozen friends now know. And in about a month I will be coming out to my “church” community, fully transitioning there so that I can dress as my new female self every Sunday at services and during my other involvements there.

I literally have a closet full of clothes now. Probably enough presentable and normal female clothing for 1-2 weeks at work. I need more shoes though (what girl doesn’t?!). And Mistress has decided that I’ll be having a second pair of ear piercings so I can wear 4 earrings at a time (like her).

Friday I’ll be talking with my gender therapist about next steps to start hormones. We’ll also go over a rough timeline. Bring it on! Let’s get this thing rolling, I’m feeling so ready to make more progress.

Mistress just used me as her urinal. “Come here, quickly!” she called from down the hall in the bathroom. I hurried in and she directed me to kneel down so she could pee in my mouth. I positioned my head and she started pissing. I quickly swallowed repeatedly to get it all down without spilling or choking. She was giggling and smiling, and when she was done she seemed pretty pleased with how it went (so to speak).

I recently bought her a GoGirl, which is a soft rubber funnel-like thing that allows women to pee standing up. No, really – see for yourself. Only about $13, reusable, portable, comfortable, and good for female domination too! You might find it at a local medical supply store. I was hoping she’d use it with me.

She said she plans to use it a lot more, particularly in our bedroom in the evenings and overnight to save her trips down the hall to the bathroom. She plans to stand next to my side of the bed, relieve herself, and then just crawl right back into bed. I guess I’ll be peeing for both of us now. She also talked about how handy it will be for traveling (no more waiting for a wayside rest stop!).

I’ve had fantasies of being used this way for many years now. Of course there are plenty of on-line stories about this. But real-life isn’t always like the fantasies. For example, daytime urine usually isn’t too terrible (depending on diet, of course). But morning pee can be pretty potent, but that’s just bonus humiliation. As with so many other things, it’s up to her now going forward.

Some irony about this occurs to me. While I’m locked in chastity, I have to pee sitting down on the toilet. Now with her GoGirl, she can pee standing up. A curious reversal.

My transgender journey continues. This week I met with the psychologist who will be coordinating my overall care, including recommendations for hormones and (hopefully eventually) surgery so that I can fully transition to be a woman.

I dressed as a female for my appointment with him and it went really well. I felt confident and comfortable, and think I did well answering his questions about my background.

I’m also interacting on-line with other transgendered folks to learn and ask questions. I shared an amazing discovery from that group with my wife earlier this week: the idea that a (transitioning) male can have a female orgasm. The idea is to provide sexual and sensual stimulation that doesn’t include the male genitals. I showed her what I read on-line, and she said “We’re going to try that – tonight!”

And we did it. I had a female orgasm. A few days later we tried again and succeeded. We were both a little surprised, in fact I went into in not really believing that I could do it. But… wow.

It really helped that my wife is bisexual – she knows how to pleasure a woman’s body She also knows what a female orgasm looks like. There’s a flushing of darker color that often happens on the neck and upper chest, followed by a whole-body experience of wave after wave of amazing feelings. And she saw me go through both.

Another fascinating effect we noticed both times: tiny (her name for my cock) wasn’t hard right before, during, or after these female orgasms. It was a different physiological experience altogether. No pre-cum, no ejaculation, not even much of an attempt at erection.

I won’t go into details of exactly what we did. I want to encourage male chastity, which is in major part about orgasm denial. Finding another way to have an orgasm while in chastity sort of defeats the purpose. Actually, I’m not sure I could accomplish it by myself anyway. The first time she had tied me to the bed, and the bondage helped me to let go.

We both noticed that my post-orgasmic attitude was different — not as crabby and male. Yet it seems tool early to report on just how that will work out longer-term. In particular, when I start taking female hormones as part of my transgender transitioning, my body is likely become even more sensitive. I’ve read that breast growth can hurt, and that nipples can be so sensitive that even clothing can feel overly intense on them. Like others, I’ll just have to deal with that (likely with a bra).

I don’t mean to make it sound like deciding to work towards a sex change is a trivial thing. It isn’t at all. This has been a life-long issue for me. My wife of 10+ years finds it easy to validate that she’s seen it in me, to some extent, all the time we’ve been together — more clearly now that our home life allows me to crossdress whenever I’m at home.

There will be a lot of upheaval in my life. I will likely be abandoned by some of my friends and family. It will be expensive and difficult in some ways. And I have never felt more comfortable, more whole, more genuine. I have some fears, but very little doubt that this is the right path for me.

Mistress woke me up this morning to use me to pleasure her to two orgasms. We were still in bed.

She started by arousing me. That turns her on, since we both know that I can’t orgasm or even have an erection being locked up as I am. She loves to torment me and watch me crave and beg for relief, knowing that the keys are in her sole control.

Once she had my attention, she sat her sexy naked body on my chest, then moved her crotch to be directly in my face. She grabbed my hair and pulled my face against her pussy. I didn’t need any further instructions, and began licking her clit.

She moved down a bit further so I could apply more pressure. Then she instructed me to bend my knees so my legs formed an incline for her to rest on. I continued lapping at her sex, and soon she had her first orgasm. I gently caressed her while she relaxed in her happy space.

She moved closer again, and my tongue found it’s way inside her. She started rotating her hand slowly on her sensitive nub while I orally penetrated her. I felt so happy to be pleasuring her. It didn’t take long for her second orgasm to wash over her. Then she rolled off, crawled back under the blankets, and instructed me to cuddle with her.

I thanked her for the opportunity to serve her. She just stroked my hair. I held her and let her enjoy her time of post-orgasmic bliss.

For my Saturday chores, Mistress let me wear my formal housekeeping dress instead of my everyday housekeeping dress. The formal one is black instead of light grey. And it looks best with black hose and black heels, instead of the white tights and white work shoes I normally wear. She complimented me on how nice the kitchen floor looked after I swept and hand-washed it on my hands and knees. I did lots of other chores too.

While changing for an evening event, she came up behind me and leaned me over the end of our bed. She played with my nipples, which arouses me intensely. I was only in my panties, and she was grinding her crotch against my ass pretending to fuck me. She kept stimulating me and I was moaning.

To my surprise she retrieved a dildo, slid a condom on it, lubed it up, and slid it inside me. Then she returned to playing with my nipples while she penetrated my behind. Again I was whining and moaning, craving release. Then she presented an even bigger surprise. She retrieved the keys to my chastity cage from the safe and tossed them on the bed.

“You’ve been such a good girl lately, I think I’ll allow tiny to squirt just once.” I wasted no time in removing the PA-lock and cage. My partial erection from all the stimulation made it difficult to pull the cage off my cock. Of course I managed. Then she was behind me sliding the dildo in and out while flicking one of my nipples with her other hand. I steadied myself with one hand and jerked off with the other, spraying a large amount of cum.

My orgasm was intense and wonderful, but it really struck me how brief it was. My legs were wobbly afterwards. I was really aware that the build-up and physical release was fleeting, and then it was gone and I was off cleaning up and putting things away. While I really enjoy those moments of pleasure, I somewhat regret how quickly they pass. My wife seems to enjoy much more time of post-orgasmic bliss.

Although she had two orgasms today and I had one, she’s had a total of five during this latest lockup. Combining this with my last round, she’s had 11 orgasms to my 2 over the last 4.5 weeks.

A couple hours later Mistress interpreted something I said as harsh and snippy. “I can sure tell that you had an orgasm.” I politely disagreed, but she wouldn’t have it. “With an attitude like that, I’m not sure I’ll ever let you have another orgasm.” I stopped disagreeing.

So, my next period of chastity begins. I hope she will use me for her pleasure again soon. If I cannot orgasm, I at least want her to be happy.